(Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile | 3695-95-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile
• 英文别名: 2-(4-nitrophenyl)-3-phenylacrylonitrile；2-(4-nitro-phenyl)-3c-phenyl-acrylonitrile；2-(4-Nitro-phenyl)-3c-phenyl-acrylonitril；α-(4-Nitro-phenyl)-cis-zimtsaeure-nitril；2-(p-Nitrophenyl)-3-phenylacrylonitrile；(Z)-2-(4-nitrophenyl)-3-phenylprop-2-enenitrile
• CAS: 3695-95-2
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: LHERNHSFIPILFV-GXDHUFHOSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  386.2±30.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile 生成
  参考文献：
  名称：

  Walkow, F.; Epperlein, J.; Mustroph, H., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 5, p. 799 - 807

  摘要：

  DOI：
• 作为产物：
  描述：

  以 水 、 二甲基亚砜 为溶剂， 生成 (Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile 、 正丁胺
  参考文献：
  名称：

  Nucleophilic addition to olefins. 8. Addition of piperidine, morpholine, and n-butylamine to .alpha.-cyano-4-nitrostilbene and .alpha.-cyano-2,4-dinitrostilbene. Kinetics and equilibria in 50% dimethyl sulfoxide-50% water

  摘要：

  DOI：

  10.1021/ja00351a038

文献信息

• Catalytic Amphiphilic Allylation via Bis-π-allylpalladium Complexes and Its Application to the Synthesis of Medium-Sized Carbocycles
  作者：Hiroyuki Nakamura、Kouichi Aoyagi、Jae-Goo Shim、Yoshinori Yamamoto

  DOI：10.1021/ja002931g

  日期：2001.1.1

  1,7-octadiene derivatives 6a−k, in good to high yields. The reaction of certain imines 9 with 4 and 5a under similar conditions as above afforded the bis-allylated amines, N-allyl-N-3-butene-1-amine derivatives 10a−f, in good to high yields. The bis-allylation reactions most probably proceed through bis-π-allylpalladium intermediate 2. The above intermolecular bis-allylation was extended to the intramolecular

  在钯催化剂的存在下，某些活化的烯烃 3 与烯丙基三丁基锡烷 (4) 和烯丙基氯 (5a) 的反应得到双烯丙基化产物，1,7-辛二烯衍生物 6a-k，产率良好至高。某些亚胺 9 与 4 和 5a 在与上述类似条件下的反应以良好至高产率提供双烯丙基化胺、N-烯丙基-N-3-丁烯-1-胺衍生物 10a-f。双烯丙基化反应最有可能通过双-π-烯丙基钯中间体2进行。上述分子间双烯丙基化反应扩展到分子内反应。8-氯-2,6-辛二烯基三丁基锡烷 (17a) 与活化烯烃 3 的反应得到区域异构环加合物、[8+2] 和 [4+2] 环加成产物的混合物。区域异构比例取决于溶剂和活化烯烃 β 位的电子密度。通常，[8+2] 环加合物 18 主要在 CH2Cl2 中获得，而 [4+2] 加合物 24 和 25 主要在 CH2Cl2 中产生。
• Direct amino acid-catalyzed cascade reductive alkylation of arylacetonitriles: high-yielding synthesis of ibuprofen analogs
  作者：Dhevalapally B. Ramachary、M. Shiva Prasad

  DOI：10.1016/j.tetlet.2010.07.131

  日期：2010.10

  A novel approach for a one-pot, three-component reductive alkylation (TCRA) reaction of arylacetonitriles-containing electron-withdrawing groups with aldehydes/ketones and 1,4-dihydropyridine via iminium-catalysis has been developed. Many TCRA reaction products have direct applications in agricultural and pharmaceutical chemistry.

  已开发出一种新的方法，用于通过亚胺基催化使含芳基乙腈的吸电子基团与醛/酮和1,4-二氢吡啶进行一锅三组分还原烷基化（TCRA）反应。许多TCRA反应产物可直接用于农业和药物化学中。
• Synthesis, Characterisation and Photophysical Properties of α,β-diaryl-acrylonitrile Derivatives
  作者：Youfeng Yue、Haiyan Fang、Meijun Wang、Zhiyuan Wang、Mingxin Yu

  DOI：10.3184/030823409x460687

  日期：2009.6

  α,β-Diarylacrylonitrile derivatives can be prepared by two different routes: (1) the intermolecular condensation of the same arylacetonitriles (2) the condensation of arylaldehydes and arylacetonitriles with a catalytic amount of NaOCH3 at room temperature. Several α,β-diarylacrylonitrile derivatives have been synthesised in this paper and characterised. The UV-vis absorption and photoluminescent (PL)

  α,β-二芳基丙烯腈衍生物可以通过两种不同的途径制备：（1）相同芳基乙腈的分子间缩合（2）芳基醛和芳基乙腈与催化量的NaOCH3在室温下缩合。本文合成并表征了几种α,β-二芳基丙烯腈衍生物。研究了产物的紫外-可见吸收和光致发光（PL）光谱。
• Efficient and reusable amine-functionalized polyacrylonitrile fiber catalysts for Knoevenagel condensation in water
  作者：Guowei Li、Jia Xiao、Wenqin Zhang

  DOI：10.1039/c2gc35483g

  日期：——

  A series of new fiber catalysts has been synthesized by aminating a commercially available polyacrylonitrile fiber with polyamines such as diethylenetriamine and triethylenetetramine. These fiber catalysts can efficiently catalyze the Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate in water (yields: 95–98%). The triethylenetetramine aminated fiber catalyst was used to catalyze the condensations of a wide range of aromatic aldehydes and active methylene compounds and in each case, this catalyst performed well with yields higher than 93%. This fiber catalyst also exhibited excellent reusability (up to 21 times) and photostability.

  通过将市售聚丙烯腈纤维与聚胺（如二亚乙基三胺和三亚乙基四胺）进行胺化，合成了一系列新型纤维催化剂。这些纤维催化剂能高效催化苯甲醛与氰乙酸乙酯在水中进行的Knoevenagel缩合反应（产率：95-98%）。三亚乙基四胺胺化纤维催化剂被用于催化多种芳香醛与活性甲基化合物之间的缩合反应，并且每种情况下，该催化剂都表现出色，产率均高于93%。此纤维催化剂还具有优异的重复使用性（可达21次）和光稳定性。
• Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols.
  作者：Francesco Fringuelli、Giosanna Pani、Oriana Piermatti、Ferdinando Pizzo

  DOI：10.1016/s0040-4020(01)89287-5

  日期：1994.1

  with benzaldehyde were studied in water in heterogeneous phase in the presence and absence of anionic and cationic surfactants such as SLS, CTACl, (CTA)2SO4 and CTAOH. All the reactions occur with excellent yields. The cationic surfactants favour the reaction and the comparison with the corresponding tetrabutylammonium salts show that the micellar catalysis is effective mainly towards the dehydration

  在存在和不存在阴离子表面活性剂和阳离子表面活性剂（例如SLS，CTACl，（CTA））的情况下，研究了苯乙醛，环己酮，异佛尔酮，苯乙腈，对硝基苯乙腈，（苯磺酰基）乙腈和茚与苯甲醛在异相水中的缩合反应。2 SO 4和CTAOH。所有反应均以优异的产率进行。阳离子表面活性剂有利于该反应，并且与相应的四丁基铵盐的比较表明，胶束催化主要对缩合之后的脱水反应有效。阴离子表面活性剂SLS是无活性的。在水性介质中以优异的产率制备了2'-羟基查耳酮，并且实现了一锅合成7-和3'，4'-取代的黄酮醇。